For many years, Montauk's First, Second, and Third Houses were the only permanent residences there for those of European descent. A traveler going on Montauk encountered the buildings in that order.
When they were built, in the 18th century, "eastern Long Islanders were graziers, rather than farmers," writes Jeannette E. Rattray in "Montauk: Three Centuries of Romance, Sport, and Adventure." The horses, sheep, and cattle that were pastured on Montauk came, she notes, from as far west as Patchogue.
The herds were rounded up, usually on May 1, to be driven east, and brought back around Nov. 1. The exact date depended on the weather and was set by the Town Trustees. It was a tradition that began in 1660 and lasted more than 275 years.
The first settlers bought Montauk from its Native American inhabitants in 1660, for use as a common pasture. At first, they took turns (two men at a time in 48-hour shifts) looking after the animals, "a regular public duty like jury duty, and not to be escaped."
In 1662, the Town Trustees decided to hire three cattle-keepers. The following year, "the first cattle yard was built, and the first shelter for the keepers," John and Stephen Hand and Isaac Hedges. "The keeper at First House had to enter all cattle on the Common Pasture list, and to repair certain fences," according to "Montauk: Three Centuries."
It was a prominent job, and housing went with it. The houses also served as shelter for travelers and hunters.
The original First House, built in 1744, stood across the road from what is today Hither Hills State Park. A new First House, built in 1798, burned down in 1909. A brick foundation and a small burying ground, still visible about 10 years ago, are all that remain; any records kept there were lost with the building.
Second House, built in 1746, was at the south end of Fort Pond. A second Second House, dating from 1797, is the one that stands today, Montauk's oldest building, on land purchased in 1968 by the Town of East Hampton and the New York State Historical Trust. The house is now a museum, run by the Montauk Historical Society.
"At Second House, the keeper looked after the sheep," writes Mrs. Rattray. Its first resident was Nathaniel Talmage, followed by Nathan Hand. In 1809, Christopher Hedges added a cellar and garden (with the Trustees' permission, of course).
Uriah Miller kept the house through the War of 1812, and became a footnote to history when sailors of the British Fleet, lying at anchor in Gardiner's Bay, raided his property and stole his cattle.
"Bravely alone except for an Indian he had forced to row him out," writes Albert R. Holden in "A Pictorial History of Montauk," he made his way to the ship, boarded it, and demanded payment. "Impressed by Miller's audacity, the British Commodore, Sir Thomas Hardy, not only paid, but declared Miller the bravest man in America!"
In 1879, while the George A. Osborns were living there, a wing was added on to Second House. The Osborns had also lived for a time at First House; they are reported to have been especially popular because Mrs. Osborn was such a good cook.
Between 1887 and 1899, George Strong Conklin kept Second House. Its last keeper was Ulysses Tillinghast Payne, whose wife established the first school in Montauk, first at First House, and then at Second House.
The original Third House, built in 1747, was at the south end of Indian Field, between Great Pond (Lake Montauk) and Oyster Pond. The building today called Third House dates from 1806 and is part of Montauk County Park. Several additions have been made through the years.
"The Third House keeper had the most important post," according to Mrs. Rattray. He had "oversight of all stock on the land, paying particular attention to the heifers and the calves; he kept the Fatting Field list, and he had to ride on Tuesday and Friday of each week among the cattle, to see that they kept in their proper fields."
Third House was the largest of the three, and had a fireplace in every room. Between 1872 and 1885 it was kept by Mr. and Mrs. Samuel Stratton, and was a popular lodging among men of wealth and gunning clubs.
An 1876 entry in the Strattons' guest book noted that "W. Gardiner and H. Sherrill, East Hampton, killed this day 69 plover east of Ditch Plain boathouse." The artist-members of the Tile Club paid a visit on June 16, 1878. Col. Theodore Roosevelt's wife and two children stayed there as well, in Rough Rider days.
The brothers Isaac and William Conklin kept Third House after 1885, and then Mr. and Mrs. Theodore Stratton. In 1896, it was taken over by Mr. and Mrs. Theodore Conklin of Amagansett, its last recorded keepers.